Triethylamine → HCID 52918885, compound

HRID 336515Notes

Reaction equation

HRID 336515 reaction equation
[OH:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([O:9][C:10]([C:12]2[CH:13]=[C:14]([CH:30]=[CH:31][CH:32]=2)[C:15]([N:17]2[C:22](=[O:23])[C:21]([F:24])=[CH:20][N:19]([CH2:25][O:26][CH2:27][CH3:28])[C:18]2=[O:29])=[O:16])=[O:11])[CH:3]=1.C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.[O:40]1[CH2:45][CH2:44]OCC1>>[CH2:10]([O:9][C:38]1[CH:39]=[C:21]([CH:37]=[C:36]([O:40][CH2:45][C:44]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[N:35]=1)[C:22]([O:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([O:9][C:10]([C:12]2[CH:13]=[C:14]([CH:30]=[CH:31][CH:32]=2)[C:15]([N:17]2[C:22](=[O:23])[C:21]([F:24])=[CH:20][N:19]([CH2:25][O:26][CH2:27][CH3:28])[C:18]2=[O:29])=[O:16])=[O:11])[CH:3]=1)=[O:23])[C:12]1[CH:13]=[CH:14][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 312751,4-Dioxane2×HCID 178468213HCID 178468213, compound

Product 1

HCID 52918885HCID 52918885, compound

Procedure

Thionyl chloride (0.23 mL) and dimethylformamide (0.01 mL) were added dropwise to a solution of Compound 2a (217 mg) obtained in Reference Example 1 and toluene (4 mL), and the mixture was stirred at 80° C. for 4.5 hours. After the resulting mixture was cooled, the solvents were evaporated. Without purification, the residual acid chloride was dissolved in dioxane (2 mL) to obtain a dioxane solution of acid chloride to be used in the following reaction. The dioxane solution of acid chloride was added dropwise under ice cooling to a solution of Compound 8a (100 mg) obtained in Reference Example 7 or Reference Example 8, triethylamine (0.01 mL) and dioxane (10 mL). The resulting mixture was stirred at room temperature for 8 hours, and the solvents were then evaporated. The resulting residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane (1:1)) to obtain Compound I-1 (119 mg).

Workup

  1. customto be used in the following reaction
  2. customthe solvents were then evaporated
  3. customThe resulting residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane (1:1))
  4. customto obtain Compound I-1 (119 mg)

Sources & evidence

ORD record
ord-1665cb3b13704f7c95bd764c7eec89a5
Source dataset
uspto-grants-2014_11
Patent number
US08889699B2

Reaction notes

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